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Zinc‐Mediated syn ‐Selective Crotylation of N‐Unsubstituted Imines
Author(s) -
Lee Won Jong,
Jeong Wook,
Park Jaiwook,
Rhee Young Ho
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600552
Subject(s) - chemistry , selectivity , zinc , yield (engineering) , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , metallurgy , materials science
The first example of a zinc‐mediated diastereoselective crotylation of N‐unsubstititued imines is described. The use of Et 3 B as an additive was of crucial importance to achieve high yield and diastereoselectivity. Notably, a high level of syn ‐selectivity was observed. A mechanism involving an open transition state is suggested to explain this unique selectivity.